Electrophotographic photosensitive member, electrophotographic apparatus, process cartridge, and method of producing electrophotographic photosensitive member

Abstract

Provided are an electrophotographic photosensitive member including a support and a photosensitive layer above the support, in which a surface layer of the electrophotographic photosensitive member includes a polymerization product of a composition containing a specific hole transporting compound, and an electrophotographic apparatus and a process cartridge including the electrophotographic photosensitive member. Also provided is a method of producing the electrophotographic photosensitive member, including (i) forming a coating film of a coating solution for a surface layer which is a composition containing a specific hole transporting compound, and (ii) forming the surface layer of the electrophotographic photosensitive member by a polymerization reaction of the composition containing the specific hole transporting compound.

What is claimed is: 
     
       1. An electrophotographic photosensitive member, comprising:
 a support; 
 a photosensitive layer above the support; and 
 a surface layer that includes a copolymerization product of a composition containing a hole transporting compound represented by Formula (1) and a compound represented by Formula (2): 
 
       
         
           
           
               
               
           
         
         where R 1  and R 2  independently represent an alkyl group having 2 to 8 carbon atoms, R 3  and R 4  independently represent a hydrogen atom or an alkyl group having 4 or less carbon atoms, R 11  and R 13  independently represent an alkylene group having 3 to 6 carbon atoms, and R 12  and R 14  independently represent a hydrogen atom or a methyl group, and 
       
       
         
           
           
               
               
           
         
         where R 21  and R 22  independently represent an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted benzyl group, the substituent of the benzyl group is an alkyl group having 4 or less carbon atoms, R 21  and R 22  may be bonded to each other to form a ring, R 23  represents an alkyl group having 1 to 4 carbon atoms, and R 24  and R 25  independently represent a hydrogen atom or a methyl group. 
       
     
     
       2. The electrophotographic photosensitive member according to  claim 1 , where R 1  and R 2  are independently an alkyl group having 2 to 5 carbon atoms, and R 11  and R 13  are each a propylene group. 
     
     
       3. The electrophotographic photosensitive member according to  claim 2 , where R 1  and R 2  are each a propyl group. 
     
     
       4. The electrophotographic photosensitive member according to  claim 1 , where at least one of R 21  and R 22  is an alkyl group having 2 or more carbon atoms. 
     
     
       5. An electrophotographic apparatus comprising: an electrophotographic photosensitive member, a charging unit, an exposing unit, a developing unit and a transfer unit, wherein
 the electrophotographic photosensitive member includes a support, a photosensitive layer above the support, and a surface layer that includes a copolymerization product of a composition containing a hole transporting compound represented by Formula (1) and a compound represented by Formula (2): 
 
       
         
           
           
               
               
           
         
         where R 1  and R 2  independently represent an alkyl group having 2 to 8 carbon atoms, R 3  and R 4  independently represent a hydrogen atom or an alkyl group having 4 or less carbon atoms, R 11  and R 13  independently represent an alkylene group having 3 to 6 carbon atoms, and R 12  and R 14  independently represent a hydrogen atom or a methyl group, and 
       
       
         
           
           
               
               
           
         
         where R 21  and R 22  independently represent an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted benzyl group, the substituent of the benzyl group is an alkyl group having 4 or less carbon atoms, R 21  and R 22  may be bonded to each other to form a ring, R 23  represents an alkyl group having 1 to 4 carbon atoms, and R 24  and R 25  independently represent a hydrogen atom or a methyl group. 
       
     
     
       6. The electrophotographic apparatus according to  claim 5 , where at least one of R 21  and R 22  is an alkyl group having 2 or more carbon atoms. 
     
     
       7. A process cartridge which integrally supports an electrophotographic photosensitive member and at least one unit selected from the group consisting of a charging unit, a developing unit, a transfer unit and a cleaning unit, and is detachably attachable to an electrophotographic apparatus main body, wherein
 the electrophotographic photosensitive member includes a support, a photosensitive layer above the support, and a surface layer that includes a copolymerization product of a composition containing a hole transporting compound represented by Formula (1) and a compound represented by Formula (2): 
 
       
         
           
           
               
               
           
         
         where R 1  and R 2  independently represent an alkyl group having 2 to 8 carbon atoms, R 3  and R 4  independently represent a hydrogen atom or an alkyl group having 4 or less carbon atoms, R 11  and R 13  independently represent an alkylene group having 3 to 6 carbon atoms, and R 12  and R 14  independently represent a hydrogen atom or a methyl group, and 
       
       
         
           
           
               
               
           
         
         where R 21  and R 22  independently represent an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted benzyl group, the substituent of the benzyl group is an alkyl group having 4 or less carbon atoms, R 21  and R 22  may be bonded to each other to form a ring, R 23  represents an alkyl group having 1 to 4 carbon atoms, and R 24  and R 25  independently represent a hydrogen atom or a methyl group. 
       
     
     
       8. The process cartridge according to  claim 7 , where at least one of R 21  and R 22  is an alkyl group having 2 or more carbon atoms. 
     
     
       9. A method of producing an electrophotographic photosensitive member including a support and a photosensitive layer above the support, the method comprising:
 (i) forming a coating film of a coating solution composition for a surface layer of the electrophotographic photosensitive member, said composition containing a hole transporting compound represented by Formula (1) and a compound represented by Formula (2): 
 
       
         
           
           
               
               
           
         
         where R 1  and R 2  independently represent an alkyl group having 2 to 8 carbon atoms, R 3  and R 4  independently represent a hydrogen atom or an alkyl group having 4 or less carbon atoms, R 11  and R 13  independently represent an alkylene group having 3 to 6 carbon atoms, and R 12  and R 14  independently represent a hydrogen atom or a methyl group, and 
       
       
         
           
           
               
               
           
         
         where R 21  and R 22  independently represent an alkyl group having 1 to 4 carbon atoms, or a substituted or unsubstituted benzyl group, the substituent of the benzyl group is an alkyl group having 4 or less carbon atoms, R 21  and R 22  may be bonded to each other to form a ring, R 23  represents an alkyl group having 1 to 4 carbon atoms, and R 24  and R 25  independently represent a hydrogen atom or a methyl group; and 
         (ii) forming the surface layer by a copolymerization reaction of the coating solution composition in the coating film. 
       
     
     
       10. The method of producing an electrophotographic photosensitive member according to  claim 9 , wherein a content of the hole transporting compound represented by Formula (1) in the coating solution composition for a surface layer is 50% by mass or more with respect to a total mass of the hole transporting compound represented by Formula (1) and the compound represented by Formula (2) in the coating solution composition for a surface layer. 
     
     
       11. The method of producing an electrophotographic photosensitive member according to  claim 9 , where at least one of R 21  and R 22  is an alkyl group having 2 or more carbon atoms.